US5919397A - Ferroelectric liquid crystal composition - Google Patents
Ferroelectric liquid crystal composition Download PDFInfo
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- US5919397A US5919397A US08/850,866 US85086697A US5919397A US 5919397 A US5919397 A US 5919397A US 85086697 A US85086697 A US 85086697A US 5919397 A US5919397 A US 5919397A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
Definitions
- the present invention relates to a ferroelectric liquid crystal composition and a liquid crystal display element employing the composition.
- the display device can exhibit only two domains which are bright and dark, respectively. In other words, it is difficult to exhibit gradation of image which is required in television display and the like. Thus, the application of the SSFLC mode at SC* phase is limited in scope considerably.
- a ferroelectric liquid crystal composition of this invention has been found by the present inventors to exhibit a novel ferroelectric liquid crystal phase that has never been reported.
- the inventors have named this novel mesophase as chiral smectic Y phase (hereinafter abbreviated to SY* phase).
- this SY* phase has a unique characteristic which other ferroelectric liquid crystal phases never have. Having made streneous efforts on research for application of this unique characteristic, the inventors have perfected the invention.
- the object of this invention is attained by
- a ferroelectric chiral smectic Y liquid crystal composition comprising at least two members selected from the group consisting of the following chiral smectic Y liquid-crystalline compounds: ##STR1##
- the object of the invention may also be attained by embodiments of the invention described in items (2) or (3).
- a ferroelectric chiral smectic Y liquid crystal composition comprising at least one first component compound selected from the group as defined in item (1), and at least one second component compound being soluble in the first component in its chiral smectic Y phase.
- a ferroelectric chiral smectic Y liquid crystal composition comprising at least one racemic mixture of the compound selected from the group as defined in item (1), and at least one optically active compound being soluble in the racemic mixture in its smectic Y phase.
- the present invention in another aspect resides in (6) a liquid crystal display element characterized by employing a chiral smectic Y phase comprising a ferroelectric chiral smectic Y liquid crystal composition as defined in any of the items (1) to (5).
- FIG. 1 shows temperature dependence characteristics of threshold voltage (Vth), dielectric constant ( ⁇ ), and spontaneous polarization (Ps) of compound (1) at its SC* and SY* phases.
- FIGS. 2(a)-2(c) each show a director vector (n) of liquid crystal molecules in the SY* phase when the applied electric field varies.
- FIG. 2(a) shows a state 1 when the applied field is lower than the threshold voltage.
- FIGS. 2(b) and 2(c) show states 2 and 3 when the impressed field is higher than the threshold voltage. The polarities of states 2 and 3 are opposite to each other.
- P and A indicate polarizer and analyzer directions, respectively.
- FIG. 3 shows optical transmittance in the SY* phase when a trianguler wave is applied.
- FIG. 4 shows optical transmittance in the SC* phase.
- FIG. 5 shows temperature dependence of electro-optic response of compound (3) in its SC* and SY* phases.
- component compound of the ferroelectric chiral smectic Y liquid crystal composition of the present invention those described in the above item (1) are preferred. Each of those compounds exhibits an SY* phase. Other liquid crystal compounds may be usable in place of those described in item (1) as far as they exhibit an SY* phase.
- a second component compound in item (2) or an optically active compound in item (3) those compounds which per se exhibit no SY* phase or no smectic Y phase (abbreviated to SY phase) but are soluble in the above-described chiral smectic Y liquid-crystalline compounds, or mixtures or racemic mixtures thereof in their SY* or SY phase to form a ferroelectric smectic Y liquid crystal mixture.
- Such compounds as may be preferably used as non-SY* component compounds in the ferroelectric liquid crystal composition of the items (2) or (3) include the following compounds. ##STR2##
- a racemic mixture of those optically active non-SY* liquid crystal compounds may also be preferred as another component of the SY* liquid crystal composition of the present invention.
- These non-SY* liquid crystal compounds exhibit no SY* phase or no SY phase, but they have a good compatibility with those chiral smectic Y liquid crystal compounds of the item (1) at their SY* and SY phases to form chiral smectic Y liquid crystal mixture. Accordingly, it is possible to reduce a content of the smectic Y or chiral smectic Y components by adding the above-described non-SY* component to the mixture, when no other non-SY* component is contained in the objective mixture.
- non-SY* or non-SY component when other non-SY* or non-SY component than the described above is contained in the composition of the invention, a content of 60% by weight or more of the SY* component is preferred.
- a content of other non-SY* component than the above-described exceeds 40% by weight, a resulting mixture has an inclination to reduce or even lose its chiral smectic Y range, which is undesirable.
- composition of the present invention described in any of the items (2) to (5) may contain non-liquid-crystalline optically active compounds or nematic compounds which have ever been used as a component of an SC* mixture for a chiral dopant or a mesomorphic range controller if they are soluble in an SY* composition.
- a novel ferroelectric smectic Y phase will be discussed hereinafter.
- Cr, SG, SF, SI, SC, SA, SF*, SI*, and Iso mean crystal, smectic G, smectic F, smectic I, smectic C, smectic A, chiral smectic F, chiral smectic I, and isotropic liquid phases, respectively.
- the compound (1) expressed by the following formula ##STR3## is a compound exhibiting an SY* phase.
- This compound has phase transition temperatures of the following.
- the compound (1) exhibits a broad SY* range between the temperatures of 65.5° C. and 118.5° C.
- a symbol S* means an unidentified chiral smectic phase.
- the above-described phase transition shows that a novel SY* phase is clearly distinguished from SC* phase, because the SC* phase is observed at an adjacent higher temperature side. Further, this SY* phase of compound (1) has no miscibility with any phases of the following compound expressed by the formula (2).
- This SY* phase has several distinctive features from those of SC* phase which had been widely studied as a typical ferroelectric liquid crystal phase.
- the SY* phase has an extremely small dielectric constant (abbreviated to ⁇ ) although the SY* phase, as the well as SC* phase, has a spontaneous polarization.
- ⁇ dielectric constant
- a small ⁇ value of a liquid crystal leads to a small electrostatic capacity of the resulting liquid crystal element which makes an electric power consumption extremely small.
- a liquid crystal display element employing an SY* phase can be driven with an extremely small power consumption compared with that required by an SC* phase of which ⁇ value is more than ten times as large as that of an SY* phase. The temperature dependence of this ⁇ value is extremely small within an SY* range.
- the SY* phase is characterized by having a varying threshold voltage (abbreviated to Vth) which is an applied least D.C. field required to align liquid crystal molecules.
- Vth varying threshold voltage
- the Vth value increases as the temperature goes down within-the SY* phase.
- FIGS. 2(a)-2(c) illustrate aligned states of liquid crystal molecules in the SY* phase by using a director vector (abbreviated to n) which is an average direction of longitudinal axes of liquid crystal molecules.
- State 1 illustrates an alignment when an applied voltage is lower than Vth.
- State 2 illustrates a director when an electric field higher than Vth is applied to the molecules according to the direction from the front surface of the drawing to the back. The direction of the applied field in state 3 is opposite to that in state 2 which is from the hack surface to the front face of the drawing.
- Aligned states of molecules at SC* phase are known to be limited to the two states of 2 and 3. An electro-optic switching phenomenon between these two stable states is used in a display element employing an SC* phase.
- FIG. 3 shows a variation of optical transmittance of a homogeneously aligned cell keeping the compound (1) in the SY* phase in the cell having a cell gap of 2 ⁇ m, when the cell is sandwiched between two polarizers perpendicularly crossed to each other and a triangular wave having a peak value of ⁇ 10 V and a period of 0.1 Hz. is impressed across the cell.
- FIG. 4 shows a variation of transmittance of the same cell in the SC* phase under the same electric field.
- the dichromatic display may exhibit a figure in two different degrees darkness or lightness for example, a black and white figure on gray ground, a white and gray figure on black ground, etc.
- the dichromatic display may be expected for a display panel for the game of Go or the reverse in which black and white figures are required together with the gray ground. Further, it becomes possible to add an indicator or an emphatic mark on a monochromatic display by introducing a third tone of darkness.
- the dichromatic display may also be applied to a light valve or a high multiplexed display panel, a traffic signal, and other outdoor display panels. The dichromatic display is expected to be used in place of a present liquid crystal display.
- This specific feature of the dichromatic display is maintained when the cell gap is widened, hence, it may have a commercial advantage over a monochromatic SSFLC mode display which can only be used with cells having a thinner cell gap.
- an optical anisotropy (abbreviated to ⁇ n) at the intermediate state 1 in FIG. 2(a) is different from those at states 2 and 3 in FIGS. 2(b) and 2(c).
- ⁇ n optical anisotropy
- compound (1) exhibits a ⁇ n of 0.11 at slate 1 and a ⁇ n of 0.16 at states 2 and 3. It has never been recognized at SC* phase that ⁇ n varies according to a state of a director of the liquid crystal molecules.
- coloration of display appearing in an electrically controlled birefringence effect mode according to retardation of transmitted light depends on the value of d ⁇ n which is the product of an optical anisotropy ( ⁇ n) and a cell gap (abbreviated to d). So, it is possible to exhibit a different color, as well as a different darkness or lightness, at state 1 from those at states 2 and 3 when a cell having a comparatively large cell gap is used.
- a combination of two colors may freely be selected to exhibit not only a dark and light dichromatic display but also a colored dichromatic display.
- a dichromatic display in three colors of orange, blue and black is available; a cell having a gap of 5 ⁇ m and keeping the same compound may exhibit three colors of purple, yellowish-green and black.
- FIG. 5 shows electro-optic response characteristics of the cell obtained in SY* and SC* phases by employing a compound expressed by the following formula (3). ##STR7##
- the electro-optic response was observed by impressing a rectangular wave of ⁇ 10 V, 50 Hz to the homogeneously aligned cell having a cell gap of 2 ⁇ m and a pair of ITO electrodes, the cell being sandwiched between two polarizer plates perpendicularly crossed to each other.
- results observed at SY* phase supercooled below the melting point are included.
- an electro-optic response is slower in a lower temperature phase than in a higher temperature phase because of a higher viscosity. It is generally known that an electro-optic response curve is discontinuous to sake a step at the phase transition point between SC* and SI* phases. On the contrary, the response curve has no such step or leap and is continuous at phase transition from SC* to SY* phases as shown in FIG. 5. Namely, it may be proposed that the response time at SY* phase is substantially the same as that at SC* phase. Additionally, a temperature dependence of response time is less in the SY* phase than in the SC* phase as illustrated in FIG. 5. This characteristic feature is one of the desired properties of a liquid crystal display element.
- a method for driving this novel liquid crystal display element includes, an SSFLC mode, as well as an electrically controlled birefringence mode in which a cell having a comparatively large cell gap is employed as mentioned before, a deformation of a helicoidal structure mode, a trangent scattering mode, a guest-host mode employing a pleochroic dye, and those display modes which are applicable to any liquid crystal cell utilized at SC* phase.
- materials for aligning films of an SY* liquid crystal cell similar materials to those used in an SC* liquid crystal cell may be used because both SY* and SC* phases have ferroelectricity.
- Such materials include polyvinyl alcohols, polyimides, silicon monoxide, silicon dioxide, polyacrylonitriles and alumina.
- ferroelectric SY* component compounds should have the same sign of Ps, while the absolute, configuration of the optically active compounds may be either sinister (S-) or rectus (R-) types.
- a liquid crystal composition A consisting of the following compounds is prepared. ##STR8## Phase transitions of each component compound is are described next to each compound. In the description, M 1 means an unidentified mesophase and SE represents a smectic E phase.
- composition exhibits phase transition temperatures of the following ##STR9## and the composition had a broad SY* range including a room temperature.
- non-SY* component compounds i.e. the fourth to sixth compounds
- SY* component compounds of the first to third compounds may be mixed with the SY* component compounds of the first to third compounds to form an SY* composition.
- This composition had a Ps of 97 nC/cm 2 at 25° C.
- SC* phase of this composition may also be used in a liquid crystal display.
- a liquid crystal composition A prepared in Example 1 was kept in a cell having a gap of 2 ⁇ m and a pair of ITO electrodes to prepare a homogeneously aligned liquid crystal element.
- a liquid crystal composition A prepared in Example 1 was kept in a cell having a gap of 4 ⁇ m and a pair of ITO electrodes to prepare a homogeneously aligned cell.
- a cell was placed between two polarizer plates crossed perpendicularly to each other and a triangular wave of ⁇ 10 V and 0.1 Hz was applied to the cell, a periodical color change having a cycle comprising dark, orange and blue colors was observed.
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US08/850,866 US5919397A (en) | 1988-02-22 | 1997-05-02 | Ferroelectric liquid crystal composition |
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
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JP63-39286 | 1988-02-22 | ||
JP63039286A JP2526085B2 (ja) | 1988-02-22 | 1988-02-22 | 強誘電性液晶組成物および液晶表示素子 |
US31293089A | 1989-02-21 | 1989-02-21 | |
US74258891A | 1991-08-07 | 1991-08-07 | |
US88830492A | 1992-05-27 | 1992-05-27 | |
US25588394A | 1994-06-07 | 1994-06-07 | |
US41888795A | 1995-04-07 | 1995-04-07 | |
US57234995A | 1995-12-14 | 1995-12-14 | |
US08/850,866 US5919397A (en) | 1988-02-22 | 1997-05-02 | Ferroelectric liquid crystal composition |
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US57234995A Continuation | 1988-02-22 | 1995-12-14 |
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US08/850,866 Expired - Fee Related US5919397A (en) | 1988-02-22 | 1997-05-02 | Ferroelectric liquid crystal composition |
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Cited By (4)
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US6317108B1 (en) * | 1992-05-22 | 2001-11-13 | Display Science, Inc. | Electrostatic video display drive circuitry and displays incorporating same |
US6692646B2 (en) | 2000-08-29 | 2004-02-17 | Display Science, Inc. | Method of manufacturing a light modulating capacitor array and product |
US8827347B2 (en) | 2010-04-23 | 2014-09-09 | Magna Mirrors Of America, Inc. | Vehicle window with shade |
US9539883B2 (en) | 2010-04-23 | 2017-01-10 | Magna Mirrors Of America, Inc. | Window with shade |
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US5184847A (en) * | 1989-06-06 | 1993-02-09 | Showa Shell Sekiyu Kabushiki Kaisha | Liquid crystal compounds |
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JPH03125119A (ja) * | 1989-10-09 | 1991-05-28 | Sharp Corp | 液晶素子の駆動方法 |
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JPH03141323A (ja) * | 1989-10-27 | 1991-06-17 | Showa Shell Sekiyu Kk | 液晶化合物 |
EP0450595B1 (en) * | 1990-04-04 | 1995-03-01 | Mitsubishi Gas Chemical Company, Inc. | Liquid crystal compound and liquid crystal display device |
DE69225010T2 (de) * | 1991-01-30 | 1998-07-30 | Mitsubishi Gas Chemical Co | Flüssigkristalline Verbindung und flüssigkristalline Anzeigevorrichtung |
US5609790A (en) * | 1992-02-04 | 1997-03-11 | Seiko Epson Corporation | Liquid crystal compositions |
JPH0665154A (ja) * | 1992-08-19 | 1994-03-08 | Showa Shell Sekiyu Kk | 液晶化合物 |
DE19509304A1 (de) * | 1994-03-16 | 1995-09-21 | Nippon Soken | Antiferroelektrische Flüssigkristallzusammensetzung |
EP0676462A1 (en) * | 1994-04-08 | 1995-10-11 | Nippon Soken, Inc. | Antiferroelectric liquid crystal composition and liquid crystal indicating element |
JPH07278059A (ja) * | 1994-04-08 | 1995-10-24 | Nippon Soken Inc | 反強誘電性液晶化合物 |
EP0678566B1 (en) | 1994-04-18 | 2001-08-29 | Nippon Soken, Inc. | Antiferroelectric liquid crystal composition |
JP3501866B2 (ja) * | 1994-07-19 | 2004-03-02 | 株式会社日本自動車部品総合研究所 | 反強誘電性液晶組成物及びそれを用いた液晶表示素子 |
JPH09165356A (ja) * | 1995-12-18 | 1997-06-24 | Mitsubishi Gas Chem Co Inc | 反強誘電性液晶化合物及び反強誘電性液晶組成物 |
JP3052817B2 (ja) * | 1995-12-28 | 2000-06-19 | 株式会社日本自動車部品総合研究所 | 反強誘電性液晶組成物 |
JPH1053765A (ja) * | 1996-06-04 | 1998-02-24 | Denso Corp | スメクチック液晶組成物及び液晶セル |
JPH1036844A (ja) * | 1996-07-25 | 1998-02-10 | Nippon Soken Inc | 反強誘電性液晶組成物 |
US6103517A (en) * | 1996-09-11 | 2000-08-15 | Mitsubishi Gas Chemical Company | Process for the production of an optically active alcohol and a novel optically active alcohol |
DE69801598T2 (de) * | 1997-01-14 | 2002-07-11 | Mitsubishi Gas Chemical Co | Flüssigkristalline Verbindung |
JPH10204036A (ja) * | 1997-01-27 | 1998-08-04 | Mitsubishi Gas Chem Co Inc | 反強誘電性液晶化合物 |
JPH10279534A (ja) * | 1997-04-07 | 1998-10-20 | Mitsubishi Gas Chem Co Inc | ラセミ化合物及びそれを含む反強誘電性液晶組成物 |
DE69801549T2 (de) * | 1997-06-20 | 2002-04-25 | Mitsubishi Gas Chemical Co | Schwalbenschwanzförmige Flüssigkristallverbindung |
DE69909193T2 (de) * | 1998-08-07 | 2004-04-15 | Mitsubishi Gas Chemical Co., Inc. | Antiferroelektrische Flüssigkristallverbindung |
US6870163B1 (en) | 1999-09-01 | 2005-03-22 | Displaytech, Inc. | Ferroelectric liquid crystal devices using materials with a de Vries smectic A phase |
US7083832B2 (en) | 2000-09-01 | 2006-08-01 | Displaytech, Inc. | Partially fluorinated liquid crystal material |
US6703082B1 (en) | 2001-06-20 | 2004-03-09 | Displaytech, Inc. | Bookshelf liquid crystal materials and devices |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6317108B1 (en) * | 1992-05-22 | 2001-11-13 | Display Science, Inc. | Electrostatic video display drive circuitry and displays incorporating same |
US6692646B2 (en) | 2000-08-29 | 2004-02-17 | Display Science, Inc. | Method of manufacturing a light modulating capacitor array and product |
US8827347B2 (en) | 2010-04-23 | 2014-09-09 | Magna Mirrors Of America, Inc. | Vehicle window with shade |
US9539883B2 (en) | 2010-04-23 | 2017-01-10 | Magna Mirrors Of America, Inc. | Window with shade |
Also Published As
Publication number | Publication date |
---|---|
JP2526085B2 (ja) | 1996-08-21 |
JPH01213390A (ja) | 1989-08-28 |
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